How to stop second-guessing yourself around women and socially.

A client of mine recently walked up to a woman in a coffee shop in Dubai.

What stood out to me was not the approach. It was what he said afterwards to me.

He never asked himself whether he should do it. It simply felt okay. Appropriate. He had no idea if she would respond well. But before any of that, he already felt he was allowed to.

The Feeling of Appropriateness

What it is

The feeling of appropriateness is a quiet, settled belief that the way you usually express yourself around women is reasonable. Even when it is not the norm around you.

It shows up when you approach someone. On a first date. In a group. When you flirt, look at a woman you find attractive, invite her somewhere, or reach for her hand.

Most men may or may not lack the skill for these things. But they lack the an internal permission. Somewhere inside, a voice says, “This is not okay for someone like me.”

Especially around women who are objectively atttactive or higher up in socio-economic hiearchy.

So how do you build that permission? In my experience, it happens in three steps.

Step 1: Look honestly at your values

Start with what you actually believe.

Some men were raised to believe that approaching or flirting with a woman goes against their faith. Others grew up hearing that a good man does not look at any woman except the one he marries.

These beliefs run deep. They come from religion, family and culture, and they are different for every person. I am not here to tell you yours are wrong.

But be honest with yourself. If your values say one thing and your desires say another, you will feel wrong every time you act. No amount of practice fixes that.

So look at this conflict first. Within yourself, and ideally with someone you trust. As long as your values and your desires are pulling in opposite directions, the rest of this process cannot really begin.

Step 2: Name your assumptions

Once your values are clear, the next barrier is your assumptions.

Assumptions are the unwritten rules you carry about what women will and will not accept. Most men never question them. They just obey them.

Many of us, especially South Asian men, carry assumptions that do more than limit how we express ourselves. They turn us into the Nice Guy. Agreeable, careful and forgettable.

Some common ones:

“I cannot look at a woman and let her notice.”
“I should not disagree with her on a first date.”
“She will be offended if I…”

Write yours down. You cannot challenge a rule you cannot see.

But naming them is not enough. An assumption rarely breaks just because you spotted it. It breaks when reality proves it wrong. Which brings us to the most important step.

Step 3: Test it in the real world

This is where the change actually happens.

Your brain will not build a new sense of what is okay from ideas alone. It needs evidence. It needs to see your new way of expressing yourself being received well, in real life.

Here is an example.

Say you believe it is inappropriate to reach for a woman’s hand on a first date. You notice the assumption. You decide to set it aside and test it.

So at some point in the date, when things feel warm, you reach for her hand.

If she holds it, something shifts. The old rule loses its grip. A little more starts to feel okay.

If she does not, you let it go easily and respect that. One no does not prove your assumption right. It is a single data point, not a verdict.

That is why this step needs volume. One attempt tells you very little. Ten, twenty, with different women and in different situations, tell you what is actually true.

Over time, your sense of what is appropriate grows. Not because someone told you it is okay, but because you have seen it for yourself.

Where this leads

That is the place my client in Dubai had reached. It did not come from a line or a technique. It came from the work underneath.

I see that a lot of guys who struggle to get dates, or cannot get past first dates, or unable to attract objectively desire women are trap in the surface level solutions, which rarely work by itself.

Some men who have an inferiority issue around certain women for whatever reasons; it may be status, race, ethnicities, personal roots primarily lack this feeling of appropriateness.

The feeling of appropriateness cannot be faked. You build it, one honest test at a time.

What about second guessing after a text, asking out, on a date, escalating, etc?

We all second guess (I guess), when we text a girl, and she doesn’t reply. We question our words, timing, vibe, and sometimes ourselves.

We second guess – how to ask her out (text or call or a DM), to use a statement or a question, etc.

In essence, our default is second guessing, especially when we really like the girl.

First of all, second guessing of this nature, is absolutely normal. Our brains, tend to feel uncomfortable in the moments of uncertainity, or when we do not have a direction.

So accept the second guessing a part of you. But the degree of seconding guessing is what matters. If second guessing is affecting the quality of the day, week and your energy, then there is a need to become alert about it.

My Solution – Accept this one axiom strongly. Repeat it again and again. Write it down multiple times

Sometimes you have to lose many battles to win a war.

Meaning – In real time, just before texting a girl or escalating, or asking someone out, or even approaching, approach the moment with the possibility that you may lose this battle, and the loss will be dissappointing, but over period of time, your capacity to be self-assured will get better.